Nogalamycin and its semisynthetic analogs are structurally unique among the anthracyclines in that the amino sugar is joined to the tetrahydronaphthacenedione nucleus through a C-C bond and through a glycosidic linkage. Several of the analogs show improved properties and promise for cancer treatment. A convergent total synthetic approach to novel analogs of nogalamycin having antitumor activity is proposed. The proposed method will allow synthesis of analogs modified in regions of the molecule, such as the amino sugar moiety, that are not readily accessible by semisynthetic methods. This first total synthesis will also settle questions about absolute configuration of the nogalamycin structure. A semisynthetic approach to new analogs modified at the quinone moiety is also proposed. Target compounds will be examined by in vitro bioassay methods and submitted to NCI for evaluation of in vivo antitumor activity.